Chris, you are a walking pro! In the old days, our weather was similar (mine being just a bit colder and winter a bit longer) but our situations for walking differed -- my walk was slightly more "urban" so I rarely wanted to wear gear.
Nowadays, my climate is different from yours (considerably warmer in winter with more rain and less snow) but my environment for walking is more similar -- a mix of paved roads without sidewalks, and trails.
Regardless, I love your system of layering -- this is basically my strategy also, except I rarely wear fleece because it makes me too hot. I like Smartwool and similar for their breathability.
I'll start a new thread for Anchie because I think my former walking outfits might work for her in her current situation. Here, I'll share what I did last winter here and some thoughts and plans going forward.
This might help anyone who lives in my Pacific Northwest climate. Useless for those of you in the northeast or midwest!
My current walks, like Chris's, are rarely urban. Yet I don't wear full on gear as a rule except for true hikes. Why? It's simple. Because I tend to go out walking at different times of day, and it's a pain to change completely from my "day" clothes! I do admit, this penchant for walking at any hour has affected my daytime clothing choices over the summer, pushing me towards a more casual style than ever. But it is what it is.
Winters here are warm (for Canada!) but often wet.
Daytime average temps in Victoria in February are about 8 or 9 C (in the 40sF), and nights can hover around -1C.
For my walks last year, I was comfortable in the following types of outfits:
First the footwear. On the worst, grubbiest days or on trails, I would in fact wear my Goretex sneakers. But more often I pulled out the Sorel sneaker boots, which are waterproof, warm, lightweight, and have enough tread for the roads and light trails. For anyone walking in suburban-ish places (or urban, for that matter) I recommend a pair of stylish but still functional winter sneaker booties like this. I am in the market for a new version. These ones are great, but too loose in the heel for me. I'll get another year from them but could use a better fitting backup.
My base layer was (depending on temps) -- a cami and undies. Wool socks. If colder out, I might wear a long sleeved base like the merino top.
Above that, a merino or cashmere sweater of some kind.
Bottoms: Usually jeans. Rarely another type of dressier trouser, simply because jeans are easier to launder and I often flick dirt up onto the backs of my pants as I walk when it is wet.
For a coat, either rainproof coat, rain resistant coat, or puffer. I have different weights of puffer for different conditions. I mostly wear the lightest one in Victoria -- rarely need the heavier ones. But there were a few days where I felt better in my warmest parka! Sometimes I would layer my raincoat over my lightweight puffer jacket.
If truly rainy, rain pants over the jeans.
Always some kind of hat if it is chilly, and gloves of some kind, and often a scarf. I like to carry a bag that allows me to remove layers and stuff them inside if I start heating up.